


Win Some, Lose Some

by AnOddSock



Category: Supernatural
Genre: Anal Sex, Blackmail, Blow Jobs, Choking, Come Swallowing, Derogatory Language, Dom Sam Winchester, Episode: s04e17 It's a Terrible Life, Extremely Dubious Consent, Face-Fucking, Face-Sitting, Felching, Gags, In Charge Sam Winchester, Kinktober, Kinktober 2018, Light Bondage, M/M, Moral Bankruptcy, Non-Canon Relationship, Non-related Sam and Dean, Office Sex, Power Play, Rape/Non-con Elements, Sex Toys, Sexual Abuse, Switch Dean Winchester, Switch Sam Winchester, Topping from the Bottom, Under-negotiated Kink, Unhealthy Relationships
Language: English
Status: Completed
Published: 2018-10-31
Updated: 2018-10-31
Packaged: 2019-08-11 02:18:09
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 4,423
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/16466810
Author URL: https://archiveofourown.org/users/AnOddSock/pseuds/AnOddSock
Summary: It's supposed to be fun, this thing between them. It started out that way. But Sam has been more and more demanding and has developed a sick fascination with Dean's throat, and mouth, and lips and all the awful things he can do to them, or with them. On his knees, under his desk, under Sam’s intense and measured gaze, Dean keeps falling apart.Sam isn’t particularly concerned with putting him back together.





	Win Some, Lose Some

**Author's Note:**

  * For [maqcy](https://archiveofourown.org/users/maqcy/gifts).



> Kintober 
> 
> 30\. **Gagging** | ~~Stockings/Tights/Pantyhose | Breast Worship~~ | **Swallowing**
> 
>  
> 
> **Maqcy prompted this:**  
>  For kinktober could I put in a teeny tiny request for day 30 with gagging and swallowing? do you remember that episode where Dean and Sam didn't know about the supernatural and it was all in an office setting? So Dean and Sam in an office setting with one of them under the desk erm gagging and swallowing. maybe person on top is a big boss and is on the phone? or any variation that floats your boat. I don't mind whether its dark like blackmail and unwilling, or enthusiastic
> 
> I went dark. I'm sure you're all very surprised by this turn of events. Voila! Enjoy my dears!

Dean had a love-hate relationship with Tuesdays. Specifically Tuesday evenings. More specifically, Tuesday nights that rolled through to the early hours of Wednesday.

He loved Tuesdays because he had the anticipation all day of his encounters with the tech guy from downstairs, Wesson. He always stayed late in the office to take international calls and he and Sam had a routine down now. Sam would come up once everyone else had left, and they’d spend the time between calls exploring each other’s bodies, seeing what noises and reactions they could pull from each other.

He hated Wednesdays because by the time midnight slipped around, Sam had always gone well passed eager and needy and straight into calculating and sadistic.

He kept trying to tell himself it was fine, it was all fine, but he knew it was a lie. Sam got bolder and harsher and more twisted week on week.

Like now for instance, with Sam obscenely reclined above him and Dean kneeling underneath his own goddamn desk. His own tie cutting into the skin of his wrists, pulling his arms forward under his own chair where they were tied around the metal post at the base of the rolling supports.

He couldn't even lean away, and no amount of fumbling had found the knots to release his hands.

Sam was looking down at him with pure delight, or was that venom? Either way, Sam was answering all his calls, pretending to be Dean for the night, and Dean was just here to service him.

He looked forward to it all day, frissons of excitement at what Sam might do to him. But these days it was never as fun or as light hearted as he hoped. Sam seemed to have dropped any pretence that Dean was also here to feel good. He was here only to find his own pleasure, more at Dean’s expense than with his cooperation. There was nothing Dean could do about it either, Sam had a hold on him that went beyond the physical and straight into the unethical — possibly even illegal, but he wasn’t sure on that one.

Not that he could think about that while he was here, enduring. Putting up with all of Sam’s crap. His knees hurt on the hard floor. His shoulders were cramping. His jaw ached. His eyes were blurry and tired from tears.

And his dick was hard as nails. No matter how much he willed it not to, his body always responded.

 _Fuck you_ he thought at his traitorous cock. _Go to hell_ he thought at Sam Wesson sitting smugly above him, in his chair.

 _Let me come_ he prayed to anyone that would listen.

Nothing had touched his cock in over an hour, and despite his arousal jumping to a thousand percent under the onslaught of humiliation, pain, and degradation, he hadn't yet been able to come untouched.

And he _needed_ it. The stress built up over the week and the teasing built up under Sam's gaze, but until Sam decided they were done - he was stuck.

Panting for breath he knelt, wanting a reprieve, a little break. Sam was finishing up a call and Dean waited for further instructions, feeling more exhausted by the second.

The pecker gag in his mouth tasted like shitty plastic, and all he could smell when he pushed closer to Sam was sweat and sex and an undercurrent of cheap cologne. The other end of the double sided gag, a six inch dildo, was half in Sam's ass, and Sam wanted him to thrust it deep, until his nose was flush to the underside of Sam's balls.

He waited, neck aching from the strain. He blinked and missed Sam's hand move, only aware of it when fingers pressed hard on the soft skin under his jaw, pushing his tongue up into the imitation penis filling his mouth.

He gagged, wanting to retch. Mouth too full to let him.

That was his cue to move and he ploughed forward as best he could.

 _Fuck you_. He thought, saliva dribbling out the side of his lips. _Fuck you hard so it can be over._

Sam moaned his name, grabbed his hair and yanked, making Dean drive forward deeper and harder.

“So good, so good, just like that.”

Dean let him set the pace, satisfied at the broken groans Sam was spewing.

“Fuck, fuck! Hit that again, just like that, faster.”

Dean followed the shouted instructions, and looked up to see more precome leaking out the slit of Sam's cock.

“Fucking perfect, little eager whore, god yeah. Do it Dean, fuck me harder. Know you can, know you love it, can't pretend you don't.”

Sam always liked to utter obscenities as his need built, it was part of his whole power trip fantasy. It was the only thing Dean didn't get off on, but it meant Sam was close so he barely ever cared.

Just a little more, and Sam would tip over the edge.

_He better fuck me, I'm not jerking off alone in the bathroom just to get release. No fucking way._

Sam's hand closed around his neck and squeezed and Dean gagged again, the plastic in his mouth squashed around his spasming throat.

He choked and Sam laughed.

 

* * *

 

Sam stopped Dean with a hand pulling on his hair, he looked up at him with a glare, and Sam laughed again. Dean been shooting daggers at him for half an hour and it hadn't stopped him from doing exactly as he pleased. He pulled Dean backwards and groaned in pleasure at the feel of the thick dildo slipping free of his ass.

He unhooked his leg from where he'd had it placed up on the desk, and reorientated his body so he could sit normally in the chair again.

“Wanna come in your mouth,” he said.

Dean rolled his eyes. But he dutifully turned his head so Sam could unbuckle the gag. It was adorable really, he was complete stuck, couldn’t even shuffle out the way, his poor bound wrists holding him exactly where Sam wanted him.

Sam used one hand to lazily undo the straps on the gag, and with the other rubbed precome up and down his cock. The pounding Dean had given his ass, the stimulation from all the hits to his prostate had want thrumming through him, his body was begging, screaming, for him to keep going — and there was no reason that undoing Dean’s gag meant he had to stop pleasuring himself.

So he worked his hand up and down, fumbled one handed with the straps, and grinned at Dean’s annoyed huffs over how long it was taking.

When the gag finally came free and Dean spit it out, Sam grabbed his chin before he could speak.

“Open up, there’s a good little hole,” he smirked.

“You ass,” Dean croaked back, and his scratchy voice went straight to Sam’s cock.

Sam nodded, and shoved his fingers into Dean’s mouth. He liked the way Dean looked when he was gagging. Got a thrill out of the sounds he made.

Dean tipped his head back, choking and spluttering, and just Sam kept shoving his fingers further, deeper, wriggling them.

Spit pooled in Dean’s mouth as Sam worked over his tongue, and rubbed up at the roof of his mouth.

“Wet for me so easily, poor little throat doesn’t like this does it?” Sam growled, one hand still pumping his own dick.

Dean made a sound of protest. Probably begging for Sam to stop, but Sam just fucked his fingers harder, quicker, sloppier as Dean drooled around him.

“We’ll get you past that reflex eventually though, don’t worry. I’ll fuck it out of you.”

He’d begun working on clearing Dean of his gag reflex weeks ago and it was slow going. Frustrating really, or it would be if he hadn’t realised how much he loved watching Dean struggle with it.

They’d started with one finger, or a slim pen, pushing it back and teaching him to relax around it. A little at a time. A little bit until Sam got bored.

He would let Dean practice a while, small things, slow thrusts, but eventually he’d want to see the real thing. And he shove half his fingers in or fuck Dean’s mouth with his cock and come while Dean’s throat fluttered and protested the intrusion.

Because sure, he’d get better at it quicker if he was given more time to really get used to it, but where was the fun in that?

Sam pulled back and let Dean swallow a few times, watching mesmerized as Dean's Adams apple bobbed. Dean looked up at him with shiny, watery eyes, and tugged on his arms.

“Are we done yet?”

“Almost,” he replied. “Want this?” he wagged his cock at Dean's face who turned his head away with a snarl of disgust.

“Don't be like that. You can't pretend you don't like it, you're drooling for it.”

He watched Dean decide not to argue, watched the resigned slump of his shoulders as he heaved a breath.

“I really fucking hate you sometimes.”

“Hate fucks can be fun too.” Sam teased.

Dean knelt with his jaw firmly shut for long seconds. Sam could outlast him, he wasn't the one uncomfortably tied on the floor after all. He lazily ran his hands over his cock and waited.

“You know,” he began eventually, “we've been doing this long enough that I can read you. I know what you want.”

Dean frowned at him, and it might have been intimidating if not for the flush in his cheeks and his eyes swimming with tears from choking.

“Your cock is desperate right now isn't it? All hard, leaking a bit? Straining.”

Dean stared at him. Loathing. Seething. Sam was hungry to make Dean look at him like that. He loved over powering Dean when Dean thought he controlled everything that went on in this office and he had plenty of ideas to keep Dean in line if he ever tried to put an end to it.

“You don't know everything.” Dean spat.

“Like what?”

“Like how I can barely look at you sometimes. How I hate this controlling persona you like to put on. I liked it better when you were just a needy bottom who liked getting fucked by his superior manager.”

“That was just foreplay,” Sam said, reaching out to cup Dean's face. “Welcome to the big leagues this is the game now.”

Dean scowled.

“My hands are numb.” He complained.

“Aww, really? My poor little superior manager doesn't like being tied up?”

“Fuck you!”

“You know how to get yourself out of this, open up, show me my favourite hole all wide and eager. Let me use you up, and then I'll untie you.”

Dean dropped his head to his chest and Sam wondered if he'd gone too far, pushed too hard and wouldn't get what he wanted the way that he wanted it. He wanted Dean to do this of his own accord, because his self hatred at enjoying it was too delicious to pass up.

Almost a minute passed but Dean lifted his head, let his jaw go slack, and leaned in.

Sam didn't waste time, he grabbed for the back of Dean's head and shoved his cock in mercilessly. Dean gagged again, tried to pull back, but Sam held firm.

He set a brutal pace, dragging Dean in quick bursts up and down his cock. It felt amazing, so hot, so wet, Sam felt the head of his cock knock against the back of Dean's throat. He felt teeth scrape the underside of the shaft, he felt Dean’s tongue trying desperately to push him out and only causing more delicious pressure.

“There you go,” Sam huffed. “Take it, let me fuck you until your throat is raw.”

Dean gagged profusely. Saliva dripped from his chin and Sam felt it every time his balls pressed up against Dean’s lips.

Sloppy, rough, wild. It was everything Sam liked. _Loved._ Everything he desired.

Almost everything.

He pulled back at the last second, “Hold open,” he gasped, “Don't you dare swallow until I say.”

He pumped his fist around his cock and emptied spurt after spurt into Dean's waiting mouth.

Some missed and landed on his chin and coated his lips, but most went in, covering his tongue and settling in his mouth.

Dean groaned. He turned bright red and closed his eyes. He really hated being a come dump and Sam knew it, that's why it was fun.

As he came down from the high of his release Sam leaned in and kissed Dean on the forehead. He placed both hands around Dean's neck and savoured the way Dean jerked at his touch. He laid one thumb on Dean's Adams apple, and the other on the soft join where jaw became throat.

He stroked languid swirls with his thumbs, brushing gently over Dean’s heated skin, pressed on Dean's Adam's apple and revelled in the spasms and noises of distress.

Dean was groaning, little sweet urging gasps as he looked wide eyed up at Sam. His jaw would be aching fiercely, the instinct to snap it closed a hard thing to keep at bay.

“Just a little longer.”

Dean shook his head. Pleading. But he always did what he was told.

“The best view in the world.” Sam sighed. “Do I look this delicious to you too?”

He inched forward until his softening cock bumped on Dean's chin.

“You beg for me quick enough you must like it.” He smirked at Dean's annoyed huffs. They both knew he'd grown to dislike the arrangement, but it didn't matter when Sam had leverage. And it was amusing to watch Dean war with himself.

Dean moaned, and his shoulders jerked, clearly reaching the end of his stamina. Knowing how to push him right to the edge was something Sam learned more and more every week.

“Keep your mouth open, but go ahead and swallow.”

Dean shook his head slightly, but complied, and Sam felt his throat work, felt the muscles force the come down. He watched as Dean struggled to swallow it all at once and had to gulp a second, and a third time, to get all of the viscous liquid to go down.

He watched it disappear from Dean's mouth, tongue working, as his hands felt the muscles inside Dean's throat contract.

He smiled. Dean never stopped being sinfully enjoyable.

 

* * *

 

Dean thought Sam would be done when he'd swallowed the cooling come. But he wasn't. He was insatiable and persistent. Dean wished he wasn't so fucking hot, then it might be easier not to in get so far over his head week after week.

Sam yanked his head back and sucked a hickey right over the top of his Adam's apple. He squirmed, gasping and grunting at the pressure. It was really going to make fastening his tie uncomfortable tomorrow. And that was probably his plan.

“Sam give over, let me the fuck up already!”

Sam licked his newest bruise, making Dean groan, and climbed out of the chair.

“You make the prettiest noises, I should record you and set you as my ringtone or something.” Sam said.

Without Sam in the way Dean could scramble round and find the knots holding his hands in place. He worked furiously trying to unpick them.

“You wouldn't dare.” and Dean hoped it was true.

Finally freeing his hands from the chair he stood up, his knees and back protesting something awful.

“I can't believe you tied me up, we didn't okay that.”

“We've done it before.”

“That may be true but who said I wanted to do it again?”

Sam shrugged and Dean wanted to throttle him.

“Maybe next time I put a gag on you you won't try and take it off and then I won’t have to.”

“We didn't talk about the gag either you fucker.”

Sam rolled his eyes. “That's why I said it was a surprise.”

“Dammit,” Dean's tie was still wrapped around his wrists pinning them together. “At least help me with this!”

“Nah, you'll figure it out, I think I'm done for the night.”

Dean saw him turn to put on his pants and leave and launched himself at Sam, grabbing hold of his t-shirt and trying to pull him off balance.

“No! No you're not leaving ‘til you take care of this,” he said, hoping his point was obvious as he couldn't really gesture right then.

“Oh so you _did_ like it.” Sam smirked.

“You are such a dick!”

He grappled with Sam trying to pull his t-shirt off over his head just in defiance of, well… everything. Sam looked so unruffled and in charge and here Dean was in his own office, treated like he had no say in anything, bruises on his knees, with chafed wrists and a fucked out throat.

Dean was still in his boxers, with his shirt undone but unable to come off past his tied arms and Sam was pantless, in nothing but a t-shirt. Dean was aware they probably looked ridiculous but he didn’t care.

“Don’t you dare leave like this, you can’t come in here and order me around and not pay me back.”

“I think I can, I think I just did,” Sam said as he fought back, pulling on the tie connected to Dean's wrists and forcing Dean in against his chest. Sam turned Dean around so they were chest to back and licked a stripe up his neck.

Dean tried to duck away but Sam wasn’t having it. He clutched Dean tight, one hand pressing on the base of his throat.

Dean was so tired of choking and gagging. He leaned back against Sam just to escape the press of the hand. Going wherever he was dragged was easier, less painful, less tiring.

“I think I come in here every week and take exactly what I want, and ignore everything I don’t. I think we both know who’s in charge here.”

Dean loathed the way he wanted to melt at the words, wanted to give over, give in.

“I just want it to be like before,” he whispered.

“You want more than that, you want what I have to offer you’re just resisting.”

God, Dean hoped that wasn’t true, he didn’t want to believe it but his body told him otherwise.

“Still, if you ask nicely, I’ll take care of your problem.”

Something in Dean curled up in mortification, the same thing that curled up and hid every time he was in this situation with Sam. His dignity noping the fuck out and leaving Dean high and dry with nothing but humiliation and need.

“Let me come,” he said.

“Was that nice?” Sam asked. He shuffled backwards, short tilting steps that kept Dean off balance. “Was that the best you’ve got? I mean I know I do better at your job than you do, but you are in communications, so _communicate_ Dean.”

Dean burned. Sam slammed him around onto the low coffee table that took up the other half of his office. Winded, surprised, Dean looked into Sam’s face and saw amusement and arousal.

He wanted to be touched, he did, all of it was so intense and his skin was screaming at him and his cock was wailing, left untouched and straining.

He closed his eyes.

“Please, Sam, come on, do it for me, please. I’ve done everything else.”

“Better.” Sam leered.

He swiped off his own shirt, straddled Dean on the table and restrained Dean’s still bound hands above his head with one of his own.

“All you have to do it beg you see, is that so hard?”

Sam grabbed for his boxers and made short work of pulling them down his thighs, making him even less able to move. Sam raised himself up, and took hold of Dean’s cock before sinking down onto it inch by inch.

Dean grit his teeth but he couldn’t keep stoic, not with the silky tight sensation of Sam’s ass swallowing his desperate cock. There was lube left from earlier, and Sam was stretched but not gaping, a hot space just made for Dean’s cock. He jerked his hips looking for more, deeper, _quicker._

In one sweep Sam stuck two fingers into Dean’s gasping mouth, forcing his head down to the table. He rolled his hips and Dean groaned as heat built in him, rising and swelling as Sam lifted up and up and then surged back down.

“You know what they say, the hardest won rewards are the best.” Sam chuckled. “Suck me like you mean it. Or I leave.”

The fingers pressed back against his tongue, crawling towards his throat and Dean practically dry heaved. He couldn’t even come in peace. Sam was everywhere, pinning him, drawing moans and gurgles out of him in equal measure.

And it was always like this, and he never wanted to be back here again, but he couldn’t seem to help himself. Even if he had a choice he thought he'd choose this, no matter how much he would hate himself for it.

Sam glared at him at stilled his undulating hips and Dean whined.

 _Please come on please_.

All he got for his meek attempts to thrust upwards — impossible to be effective with Sam's weight pinning him down — was raised eyebrows and an expectant look.

He closed his eyes and started working his tongue, his lips, massaging Sam's fingers and jerking when they pressed too far back. He suckled like they were the best thing he’d ever tasted and his tired mind crawled further away from caring about how pathetic it was out of shame.

Sam grinned ferally and resumed his steady pace, fucking himself on Dean's cock with glee.

By the time he came Dean was a panting, exhausted collection of limbs and tattered thoughts. His hands throbbed. His tie was probably ruined, it had been twisted around for hours. His arms ached from being held ruthlessly above his head.

Sam slid off him with a pleasured gasp, winking when Dean lifted his eyes to his.

“Love having you in me, you know,” he said as he shuffled further up Dean’s chest.

“Good for you, now get _off._ ”

“I would but see I don’t wanna go home a mess, and you made quite a mess.”

“Well you know where the bathroom is, jackass.”

“Yeah, but you’re right here.”

Sam moved, quick as a flash, and Dean didn’t know how the guy still had energy left. He straddled Dean’s upper body, and Dean got one horrible second to process what was coming before Sam was practically sitting on his face.

He had to close his eyes, or get an eye full of pubes and Sam’s balls pressing over the bridge of his nose.

He cried out a muffled plea which made Sam laugh.

Sam ground his hips down and his ass was millimetres from Dean’s mouth. His ass which was decidedly sticky. Dean felt come dripping onto his chin and clamped his jaw shut.

“No!” he yelled through his teeth.

“Do it Dean, my plaything, my good little fuck buddy.”

Dean shook his head. Praying, hoping, that Sam would just up and leave, he was so far beyond done.

“Clean me up, you good for nothing _fuck_ ,” Sam said and cruelly twisted one of Dean’s nipples. “Or do you want me to start telling people about all of our hook ups? Tell them how badly you want to be ordered around and get on your knees?”

Dean let out a huff of breath, because there it was again. The thing Sam kept threatening every time he attempted to refuse another degrading thing, and it wasn’t hard to see how badly it could reflect on him. His career here would be over, company policy forbid any fraternizing between any employees, the fact he was technically Sam's boss would make it even worse.

And he definitely hated the thought of anyone knowing the details of this fucked up dynamic between them. His reputation might be sullied, his friends might abandon him, his life could change unfathomably.

And Sam held it all in his hands, literally too, Dean knew he had pictures, and messages saved.

Dean had hoped at first that it was a one off, hoped it had been a hot headed moment of anger. Apparently not. Sam kept reminding him, holding the horror of being outed to the whole company, the whole _world_ , over his head. Using it to see how far Dean would jump to avoid having his life destroyed.

“I’m waiting.”

Dean gasped and bucked at another harsh twist to his nipple, but tentatively stuck out his tongue. He tasted his own come and wanted to retch.

Sam moaned, and pushed his ass even lower.

“Get it all, use your lips too, suck it out.”

Dean steeled himself, and got to work.

 

* * *

 

As they rode the elevator down to the ground floor Dean checked out his new assortment of bruises in the mirrored walls.

“You really did a number on me.”

He didn't particularly care if Sam heard or not.

Sam crowded into his space and nuzzled at the back of his neck, bending down to reach. It was almost sweet. It was soft, until there was a graze of teeth along the nape of his neck.

“I like marking you. I like knowing you have little reminders of me.”

Dean nodded. He kind of liked it too. And he hated that any part of him thought that.

“Same time next week.” Sam declared as the doors pinged open.

Dean nodded again. He was boxed into a corner, and even when Sam smiled against his cheek and left, the claustrophobic feeling stayed with him.

If he didn't turn up and put out Sam might go through with his threatening promises, and there was no way that ended well.

His first meeting the next morning wasn't until ten am, so he had a few hours to grab ineffectually at sleep, to attempt to recover and feel clean.

And he had a week to figure out if there was a way to fix it but his blood pumped faster in excitement just from thinking about being near Sam again.

Maybe he was as fucked up and desperate as Sam said. Maybe it wasn't so bad after all. Maybe he needed exactly what he was getting.

Maybe it didn't make a damn bit of difference either way.

**Author's Note:**

> I’m really pleased with this one, the idea crawled under my skin and snuggled up to stay. The best kind of parasite.
> 
> Let me know if you liked it, comments and kudos make me love you forever!


End file.
